EP3946639A1 - Compositions d'hygiene buccale et leurs méthodes d'utilisation - Google Patents

Compositions d'hygiene buccale et leurs méthodes d'utilisation

Info

Publication number
EP3946639A1
EP3946639A1 EP19926062.1A EP19926062A EP3946639A1 EP 3946639 A1 EP3946639 A1 EP 3946639A1 EP 19926062 A EP19926062 A EP 19926062A EP 3946639 A1 EP3946639 A1 EP 3946639A1
Authority
EP
European Patent Office
Prior art keywords
composition
mesa
composition according
methyl salicylate
compositions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19926062.1A
Other languages
German (de)
English (en)
Other versions
EP3946639A4 (fr
Inventor
Erin LASKOWSKI
Victoria YEUNG
Mania BANKOVA
Long Pan
Yun Xu
Peng Yan
Fusong SUN
Zheng Yang
Chi-Yuan Cheng
Tatiana BRINZARI
Zhigang Hao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Publication of EP3946639A1 publication Critical patent/EP3946639A1/fr
Publication of EP3946639A4 publication Critical patent/EP3946639A4/fr
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A61K8/21—Fluorides; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • compositions capable of stabilizing one or more flavor components.
  • the oral care compositions of the present disclosure comprise an amino acid, and a flavor containing methyl salicylate, as well as to methods of making these compositions.
  • Methyl salicylate is a component in Wintergreen oil, and has been extensively used as a flavor agent in many consumer products, such as a mouth rinse, toothpaste, body lotions and creams.
  • MeSA is also an important ester compound that has been widely used in food, cosmetic and pharmaceutical industries as flavorant, solvents, preservatives, and perfumes.
  • MeSA has a phenolic hydroxyl group at the ortho position, and has an intramolecular hydrogen bond between its hydroxyl and carbonyl groups.
  • Optical spectroscopic studies have shown that MeSA can have different conformers with six-member rings through the formation of a strong intramolecular hydrogen bond, whose structures were considered to be energetically more stable than the non-hydrogen-bonded one in these compounds.
  • Flavors are very critical components in oral care products, often making the first and most important impression upon a consumer.
  • One particularly popular principal flavor used in toothpastes and mouthwashes is Wintergreen.
  • Methyl salicylate (MeSA) a major flavor component in Wintergreen oil, has in fact been extensively used in a variety of consumer products.
  • the ester moiety of MeSA can be easily hydrolyzed in aqueous solution through a well-known mechanism via either acidic or alkaline hydrolysis. Alkaline hydrolysis of MeSA at raising temperature and in organic media to improve MeSA solubility has been previously reported.
  • MeSA hydrolysis in aqueous solution at room temperature is still unclear due to its poor water solubility.
  • compositions and related methods of making and use are needed for the stabilization of MeSA.
  • compositions and related methods are needed for stabilizing MeSA, and therefore Wintergreen flavoring, in compositions containing amino acid ingredients.
  • compositions and related methods of making and use for the stabilization of MeSA have created compositions and related methods of making and use for the stabilization of MeSA.
  • the inventors have created compositions and related methods for stabilizing MeSA, and therefore Wintergreen flavoring or other flavorings containing MeSA, in compositions containing amino acid ingredients. Therefore, the presently disclosed compositions maintain a high level of consumer acceptance.
  • an oral care composition comprising:
  • composition has a pH of 6.0-8.0.
  • Figure 1 illustrates 1 H NMR spectra of a tested sample contained 0.05 wt% (3.29 mM) methyl salicylate (MeSA) and 0.025 wt%glycine (Gly) as a function of hydrolysis time at 25°C.
  • MeSA methyl salicylate
  • Gly 0.025 wt%glycine
  • Figure 2 illustrates the time-dependence of methyl salicylate (MeSA) degradation compared with salicylic acid and methanol formation in the sample contained 0.05%methyl salicylate and 0.025%glycine (Gly) at pH 9.0 at 25°C.
  • MeSA methyl salicylate
  • Figure 3 illustrates the time course of methyl salicylate content (without amino acid) in the sample at various pH.
  • Figure 4 illustrates the time course of methyl paraben, methyl benzoate, and methyl salicylate with and without glycine at pH 9.0.
  • Figure 5 illustrates 1 H NMR chemical shift of MeSA and MeSA + Glycine (Gly) freshly prepared sample (1 ⁇ 1) at pH 9.0 prior to hydrolysis.
  • Figure 6 illustrates the time course of methyl salicylate content in the presence of glycine at different glycine: MeSA ratios at pH 9.0.
  • Figure 7 illustrates the time course of methyl salicylate content with different protective glycine derivatives at pH 9.0.
  • Figure 8 illustrates the time course of methyl salicylate content with lysine and arginine at pH 9.0.
  • Figure 9 illustrates the methyl salicylate concentration in the presence or absence of arginine after 1 week aged at 40°C measured by UV/Vis.
  • Figure 10 illustrates the mass spectrum detailing the components in wintergreen oil.
  • oral composition means the total composition that is delivered to the oral surfaces.
  • the composition is further defined as a product which, during the normal course of usage, is not, the purposes of systemic administration of particular therapeutic agents, intentionally swallowed but is rather retained in the oral cavity for a time sufficient to contact substantially all of the dental surfaces and/or oral tissues for the purposes of oral activity.
  • examples of such compositions include, but are not limited to, toothpaste or a dentifrice, a mouthwash or a mouth rinse, a topical oral gel, a denture cleanser, sprays, powders, strips, floss and the like.
  • dentifrice means paste, gel, or liquid formulations unless otherwise specified.
  • the dentifrice composition can be in any desired form such as deep striped, surface striped, multi-layered, having the gel surrounding the paste, or any combination thereof.
  • the oral composition may be dual phase dispensed from a separated compartment dispenser.
  • composition 1 comprising:
  • composition has a pH of 6.0-8.0.
  • compositions contemplates any of the following compositions (unless otherwise indicated, values are given as percentage of the overall weight of the composition) :
  • composition 1 wherein the amino acid is selected from the group consisting of arginine, lysine, and/or glycine.
  • composition 1 or 1.1 wherein the amino acid is arginine.
  • composition 1 or 1.1 wherein the amino acid is glycine.
  • compositions wherein the basic amino acid has the L-configuration (e.g., L-arginine) .
  • compositions wherein the amino acid is provided in the form of a di-or tri-peptide comprising arginine, or salts thereof.
  • compositions wherein the amino acid is arginine, and wherein the arginine is present in an amount corresponding to 0.1%to 10%, e.g., 0.1 wt. %to 3.0 wt. %of the total composition weight, about e.g., 0.5%, 1.0%1.5%, 2.0%, 2.5%, or 3.0%, wherein the weight of the basic amino acid is calculated as free form.
  • compositions wherein the amino acid is arginine from 0.1 wt. %to 3.0 wt. %. (e.g., about 1.5 wt%) .
  • compositions wherein the amino acid is arginine from about 1.5 wt. %.
  • compositions wherein the amino acid is arginine in partially or wholly in salt form.
  • compositions wherein the amino acid is arginine ionized by neutralization with an acid or a salt of an acid.
  • wintergreen flavor is wintergreen oil and comprising members selected from the group consisting of methyl salicylate, menthol, anethole, eugenol or combinations thereof.
  • wintergreen flavor is wintergreen oil comprising methyl salicylate, menthol, anethol, and eugenol.
  • wintergreen flavor is wintergreen oil comprising methyl salicylate.
  • compositions wherein the wintergreen flavor is present in an amount of about 0.1 to 5.0 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the wintergreen flavor is present in an amount of about 0.1 to 3.0 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the wintergreen flavor is present in an amount of about 0.1 to 2.0 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the wintergreen flavor is present in an amount of about 1.0 to 2.0 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the wintergreen flavor is present in an amount of about 1.0 to 1.5 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the wintergreen flavor is present in an amount of about 1.25 wt. %, calculated relative to the total weight of the composition.
  • compositions wherein the composition does not contain any further flavoring agents.
  • compositions capable of stabilizing the methyl salicylate such that less than 50%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions (i.e., 49°C environment) , less than 45%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions, less than 40%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions, less than 35%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions, or less than 30%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions.
  • accelerated aging conditions i.e., 49°C environment
  • compositions capable of stabilizing the methyl salicylate such that only 32%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions (i.e., 49°C environment) .
  • compositions capable of stabilizing the methyl salicylate such that only 28%of the methyl salicylate degrades after 6 weeks under accelerated aging conditions (i.e., 49°C environment) .
  • compositions wherein the abrasive or particulate is selected from alumina, aluminum hydroxide, calcium carbonate, precipitated calcium carbonate, dicalcium phosphate, mica, sodium bicarbonate, calcium pyrophosphate or combinations thereof.
  • compositions wherein the abrasive or particulate is a calcium abrasive.
  • abrasive or particulate is a calcium abrasive selected from the group consisting of calcium carbonate, precipitated calcium carbonate, dicalcium phosphate calcium pyrophosphate or combinations thereof.
  • compositions wherein the abrasive or particulate is present in an amount of about 10 to 90 wt. %, about 20 to 70 wt. %, about 30 to 50 wt. %, or about 35 to 45 wt. % (e.g., about 40%) , calculated relative to the total weight of the composition.
  • compositions wherein the abrasive or particulate is present in an amount of about 30 to 50 wt. % (e.g., about 40%) , calculated relative to the total weight of the composition.
  • compositions wherein the abrasive or particulate is present in an amount of about 35 to 45 wt. % (e.g., about 40%) , calculated relative to the total weight of the composition.
  • compositions wherein the abrasive or particulate is present in an amount of about 40%, calculated relative to the total weight of the composition.
  • compositions comprising silica wherein the silica is used as a thickening agent, e.g., particle silica.
  • the orally acceptable vehicle comprises one or more of water, a thickener, a buffer, a humectant, a surfactant, a sweetener, a pigment, a dye, an anti-caries agent, an anti-bacterial, a whitening agent, a desensitizing agent, a vitamin, a preservative, an enzyme, and mixtures thereof.
  • compositions wherein the composition comprises a humectant selected from glycerine, sorbitol, xylitol, propylene glycol or combinations thereof.
  • compositions comprising a humectant in an amount of 15 to 70 wt. %or 30 to 65 wt %, based on the total weight of the composition.
  • compositions further comprising a fluoride source selected from: sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride (e.g., N′-octadecyltrimethylendiamine-N, N, N′-tris (2-ethanol) -dihydrofluoride) , ammonium fluoride, titanium fluoride, hexafluorosulfate, and combinations thereof.
  • a fluoride source selected from: sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride (e.g., N′-octadecyltrimethylendiamine-N, N, N′-tris (2-ethanol) -dihydrofluoride) , ammonium fluoride, titanium fluoride, hexafluorosulfate, and combinations thereof.
  • compositions wherein the composition comprises a fluoride source present in an amount of 0.01 wt. %to 2 wt. % (e.g., 0.1 wt%-1.0 wt. %) of the total composition weight.
  • compositions wherein the composition comprises more than one fluoride source.
  • compositions wherein the composition comprises a combination of sodium fluoride and sodium monofluorophosphate.
  • compositions comprising a combination of sodium fluoride present in an amount of about 0.01 to 0.2 wt %, based on the total weight of the composition, and sodium monofluorophosphate present in an amount of about 0.5 to 1.0 wt. %, based on the total weight of the composition.
  • compositions further comprising an effective amount of one or more alkali phosphate salts, e.g., sodium, potassium or calcium salts, e.g., selected from alkali dibasic phosphate and alkali pyrophosphate salts, e.g., alkali phosphate salts selected from sodium phosphate dibasic, potassium phosphate dibasic, dicalcium phosphate dihydrate, calcium pyrophosphate, tetrasodium pyrophosphate, tetrapotassium pyrophosphate, sodium tripolyphosphate, disodium hydrogenorthophoshpate, monosodium phosphate, pentapotassium triphosphate and mixtures of any of two or more of these, e.g., in an amount of0.01-20%, e.g., 0.1-8%, e.g., e.g., 0.1 to 5%, e.g., 0.3 to 2%, e.g., e.g.,
  • compositions comprising tetrapotassium pyrophosphate, disodium hydrogenorthophoshpate, monosodium phosphate, and pentapotassium triphosphate.
  • compositions comprising a polyphosphate.
  • composition wherein the tetrasodium pyrophosphate is from 0.01 -1.0 wt% (e.g., about 0.25 wt%) .
  • compositions further comprising a nonionic surfactant, wherein the nonionic surfactant is in an amount of from 0.5 -5%, selected from poloxamers (e.g., poloxamer 407) , polysorbates (e.g., polysorbate 20) , polyoxyl hydrogenated castor oil (e.g., polyoxyl 40 hydrogenated castor oil) , and mixtures thereof.
  • a nonionic surfactant selected from poloxamers (e.g., poloxamer 407) , polysorbates (e.g., polysorbate 20) , polyoxyl hydrogenated castor oil (e.g., polyoxyl 40 hydrogenated castor oil) , and mixtures thereof.
  • the poloxamer nonionic surfactant has a polyoxypropylene molecular mass of from 3000 to 5000 g/mol and a polyoxyethylene content of from 60 to 80 mol%, e.g., the poloxamer nonionic surfactant comprises poloxamer 407.
  • compositions further comprising sorbitol, wherein the sorbitol is in a total amount of 10-40% (e.g., about 23%) .
  • compositions further comprising a zinc ion source selected from zinc oxide, zinc citrate, zinc lactate, zinc phosphate and combinations thereof.
  • composition wherein the zinc ion source comprises or consists of a combination of zinc oxide and zinc citrate.
  • composition wherein the ratio of the amount of zinc oxide (e.g., wt. %) to zinc citrate (e.g., wt%) is from 1.5: 1 to 4.5: 1 (e.g., 2: 1, 2.5: 1, 3: 1, 3.5: 1, or 4: 1) .
  • compositions wherein the zinc ion source comprises zinc citrate in an amount of about about 0.5 wt%.
  • compositions wherein the zinc ion source comprises zinc oxide in an amount of about 1.0 wt%.
  • compositions wherein the zinc ion source comprises zinc citrate in an amount of about about 0.5 wt%and zinc oxide in an amount of about 1.0 wt%.
  • compositions further comprising an additional ingredient selected from: benzyl alcohol, Methylisothizolinone ( “MIT” ) , Sodium bicarbonate, sodium methyl cocoyl taurate (tauranol) , lauryl alcohol, and polyphosphate.
  • benzyl alcohol Methylisothizolinone ( “MIT” )
  • MIT Methylisothizolinone
  • Sodium bicarbonate sodium methyl cocoyl taurate
  • lauryl alcohol lauryl alcohol
  • polyphosphate polyphosphate
  • composition further comprises a copolymer.
  • the PVM/MA copolymer comprises a 1 ⁇ 4 to 4 ⁇ 1 copolymer of maleic anhydride or acid with a further polymerizable ethylenically unsaturated monomer; for example, 1 ⁇ 4 to 4 ⁇ 1, e.g. about 1 ⁇ 1.
  • compositions 1.50-1.52 wherein the PVM/MA copolymer comprises a copolymer of methyl vinyl ether/maleic anhydride, wherein the anhydride is hydrolyzed following copolymerization to provide the corresponding acid.
  • compositions wherein the composition comprises a thickening agent selected from the group consisting of carboxyvinyl polymers, carrageenan, xanthan, hydroxyethyl cellulose and water soluble salts of cellulose ethers (e.g., sodium carboxymethyl cellulose and sodium carboxymethyl hydroxyethyl cellulose) .
  • a thickening agent selected from the group consisting of carboxyvinyl polymers, carrageenan, xanthan, hydroxyethyl cellulose and water soluble salts of cellulose ethers (e.g., sodium carboxymethyl cellulose and sodium carboxymethyl hydroxyethyl cellulose) .
  • compositions further comprising sodium carboxymethyl cellulose (e.g., from 0.5 wt. %-1.5 wt. %) .
  • compositions comprising from 5%-40%, e.g., 10%-35%, e.g., about 15%, 25%, 30%, and 35%water.
  • compositions comprising an additional antibacterial agent selected from halogenated diphenyl ether (e.g. triclosan) , herbal extracts and essential oils (e.g., rosemary extract, tea extract, magnolia extract, thymol, menthol, eucalyptol, geraniol, carvacrol, citral, honokiol, catechol, methyl salicylate, epigallocatechin gallate, epigallocatechin, gallic acid, miswak extract, sea-buckthorn extract) , bisguanide antiseptics (e.g., chlorhexidine, alexidine or octenidine) , quaternary ammonium compounds (e.g., cetylpyridinium chloride (CPC) , benzalkonium chloride, tetradecylpyridinium chloride (TPC) , N-tetradecyl-4-ethylpyridinium chloride (TDEPC) ,
  • compositions comprising an antioxidant, e.g., selected from the group consisting of Co-enzyme Q10, PQQ, Vitamin C, Vitamin E, Vitamin A, BHT, anethole-dithiothione, and mixtures thereof.
  • an antioxidant e.g., selected from the group consisting of Co-enzyme Q10, PQQ, Vitamin C, Vitamin E, Vitamin A, BHT, anethole-dithiothione, and mixtures thereof.
  • compositions comprising a whitening agent.
  • compositions comprising a whitening agent selected from a whitening active selected from the group consisting of peroxides, metal chlorites, perborates, percarbonates, peroxyacids, hypochlorites, and combinations thereof.
  • a whitening agent selected from a whitening active selected from the group consisting of peroxides, metal chlorites, perborates, percarbonates, peroxyacids, hypochlorites, and combinations thereof.
  • compositions further comprising hydrogen peroxide or a hydrogen peroxide source, e.g., urea peroxide or a peroxide salt or complex (e.g., such as peroxyphosphate, peroxycarbonate, perborate, peroxysilicate, or persulphate salts; for example, calcium peroxyphosphate, sodium perborate, sodium carbonate peroxide, sodium peroxyphosphate, and potassium persulfate) , or hydrogen peroxide polymer complexes such as hydrogen peroxide-polyvinyl pyrrolidone polymer complexes.
  • urea peroxide or a peroxide salt or complex e.g., such as peroxyphosphate, peroxycarbonate, perborate, peroxysilicate, or persulphate salts; for example, calcium peroxyphosphate, sodium perborate, sodium carbonate peroxide, sodium peroxyphosphate, and potassium persulfate
  • hydrogen peroxide polymer complexes such as hydrogen peroxide-polyvin
  • compositions further comprising an agent that interferes with or prevents bacterial attachment, e.g. ethyl lauroyl arginiate (ELA) or chitosan.
  • an agent that interferes with or prevents bacterial attachment e.g. ethyl lauroyl arginiate (ELA) or chitosan.
  • oral composition may be any of the following oral compositions selected from the group consisting of: a toothpaste or a dentifrice, a mouthwash or a mouth rinse, a topical oral gel, sprays, powders, strips, floss and a denture cleanser.
  • composition obtained or obtainable by combining the ingredients as set forth in any of the preceding compositions.
  • the present disclosure also provides for a composition obtained or obtainable by combining the ingredients as set forth in any of the preceding compositions.
  • compositions for use as set forth in any of the preceding compositions.
  • the present disclosure provides for a method of stabilizing one or more flavoring components in an oral care composition, comprising providing a composition according to Composition 1, et seq.
  • the invention further comprises the use of an amino acid and a flavoring component comprising methyl salicylate in the manufacture of a Composition of the Invention, e.g., for use in any of the indications set forth in the above method of Composition 1, et seq.
  • the oral care compositions may further include one or more fluoride ion sources, e.g., soluble fluoride salts.
  • fluoride ion sources e.g., soluble fluoride salts.
  • fluoride ion-yielding materials can be employed as sources of soluble fluoride in the present compositions. Examples of suitable fluoride ion-yielding materials are found in U.S. Pat. No. 3,535,421, to Briner et al.; U.S. Pat. No. 4,885,155, to Parran, Jr. et al. and U.S. Pat. No. 3,678,154, to Widder et al., each of which are incorporated herein by reference.
  • Representative fluoride ion sources used with the present invention include, but are not limited to, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, and combinations thereof
  • the fluoride ion source includes sodium fluoride, sodium monofluorophosphate as well as mixtures thereof.
  • the fluoride salts are preferably salts wherein the fluoride is covalently bound to another atom, e.g., as in sodium monofluorophosphate, rather than merely ionically bound, e.g., as in sodium fluoride.
  • the invention may in some embodiments contain anionic surfactants, e.g., the Compositions of Composition 1.0, et seq., for example, water-soluble salts of higher fatty acid monoglyceride monosulfates, such as the sodium salt of the monosulfated monoglyceride of hydrogenated coconut oil fatty acids such as sodium N-methyl N-cocoyl taurate, sodium cocomo-glyceride sulfate; higher alkyl sulfates, such as sodium lauryl sulfate; higher alkyl-ether sulfates, e.g., of formula CH 3 (CH 2 ) m CH 2 (OCH 2 CH 2 ) n OS0 3 X, wherein m is 6-16, e.g., 10, n is 1-6, e.g., 2, 3 or 4, and X is Na or, for example sodium laureth-2 sulfate (CH 3 (CH2) 10 CH 2 (OCH 2 CH 2 ) 2 OS
  • the anionic surfactant (where present) is selected from sodium lauryl sulfate and sodium ether lauryl sulfate.
  • the anionic surfactant is present in an amount which is effective, e.g., > 0.001%by weight of the formulation, but not at a concentration which would be irritating to the oral tissue, e.g., 1%, and optimal concentrations depend on the particular formulation and the particular surfactant.
  • the anionic surfactant is present at from 0.03%to 5%by weight, e.g., 1.5%.
  • cationic surfactants useful in the present invention can be broadly defined as derivatives of aliphatic quaternary ammonium compounds having one long alkyl chain containing 8 to 18 carbon atoms such as lauryl trimethylammonium chloride, cetyl pyridinium chloride, cetyl trimethylammonium bromide, di-isobutylphenoxyethyldimethylbenzylammonium chloride, coconut alkyltrimethylammonium nitrite, cetyl pyridinium fluoride, and mixtures thereof.
  • Illustrative cationic surfactants are the quaternary ammonium fluorides described in U.S. Pat. No. 3,535,421, to Briner et al., herein incorporated by reference. Certain cationic surfactants can also act as germicides in the compositions.
  • Illustrative nonionic surfactants of Composition 1.0, et seq., that can be used in the compositions of the invention can be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound which may be aliphatic or alkylaromatic in nature.
  • nonionic surfactants include, but are not limited to, the Pluronics, polyethylene oxide condensates of alkyl phenols, products derived from the condensation of ethylene oxide with the reaction product of propylene oxide and ethylene diamine, ethylene oxide condensates of aliphatic alcohols, long chain tertiary amine oxides, long chain tertiary phosphine oxides, long chain dialkyl sulfoxides and mixtures of such materials.
  • the composition of the invention comprises a nonionic surfactant selected from polaxamers (e.g., polaxamer 407) , polysorbates (e.g., polysorbate 20) , polyoxyl hydrogenated castor oils (e.g., polyoxyl 40 hydrogenated castor oil) , betaines (such as cocamidopropylbetaine) , and mixtures thereof.
  • a nonionic surfactant selected from polaxamers (e.g., polaxamer 407) , polysorbates (e.g., polysorbate 20) , polyoxyl hydrogenated castor oils (e.g., polyoxyl 40 hydrogenated castor oil) , betaines (such as cocamidopropylbetaine) , and mixtures thereof.
  • Illustrative amphoteric surfactants of Composition 1.0, et seq., that can be used in the compositions of the invention include betaines (such as cocamidopropylbetaine) , derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be a straight or branched chain and wherein one of the aliphatic substituents contains about 8-18 carbon atoms and one contains an anionic water-solubilizing group (such as carboxylate, sulfonate, sulfate, phosphate or phosphonate) , and mixtures of such materials.
  • betaines such as cocamidopropylbetaine
  • the surfactant or mixtures of compatible surfactants can be present in the compositions of the present invention in 0.1%to 5%, in another embodiment 0.3%to 3%and in another embodiment 0.5%to 2%by weight of the total composition.
  • the oral care compositions of the invention may also include a flavoring agent.
  • Flavoring agents which are used in the practice of the present invention include, but are not limited to, essential oils and various flavoring aldehydes, esters, alcohols, and similar materials, as well as sweeteners such as sodium saccharin.
  • the essential oils include oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, grapefruit, and orange. Also useful are such chemicals as menthol, carvone, and anethole. Certain embodiments employ the oils of peppermint and spearmint.
  • the flavoring agent is incorporated in the oral composition at a concentration of 0.01 to 1%by weight.
  • the oral care compositions of the invention also may include one or more chelating agents able to complex calcium found in the cell walls of the bacteria. Binding of this calcium weakens the bacterial cell wall and augments bacterial lysis.
  • the pyrophosphate salts used in the present compositions can be any of the alkali metal pyrophosphate salts.
  • salts include tetra alkali metal pyrophosphate, dialkali metal diacid pyrophosphate, trialkali metal monoacid pyrophosphate and mixtures thereof, wherein the alkali metals are sodium or potassium.
  • the salts are useful in both their hydrated and unhydrated forms.
  • An effective amount of pyrophosphate salt useful in the present composition is generally enough to provide least 0.1 wt.
  • %pyrophosphate ions e.g., 0.1 to 3 wt 5, e.g., 0.1 to 2 wt%, e.g., 0.1 to 1 wt%, e.g., 0.2 to 0.5 wt%.
  • the pyrophosphates also contribute to preservation of the compositions by lowering water activity.
  • the oral care compositions of the invention also optionally include one or more polymers, such as polyethylene glycols, polyvinyl methyl ether maleic acid copolymers, polysaccharides (e.g., cellulose derivatives, for example carboxymethyl cellulose, or polysaccharide gums, for example xanthan gum or carrageenan gum) .
  • polysaccharides e.g., cellulose derivatives, for example carboxymethyl cellulose, or polysaccharide gums, for example xanthan gum or carrageenan gum
  • Acidic polymers for example polyacrylate gels, may be provided in the form of their free acids or partially or fully neutralized water soluble alkali metal (e.g., potassium and sodium) or ammonium salts.
  • Certain embodiments include 1: 4 to 4: 1 copolymers ofmaleic anhydride or acid with another polymerizable ethylenically unsaturated monomer, for example, methyl vinyl ether (methoxyethylene) having a molecular weight (M.W. ) of about 30,000 to about 1,000,000.
  • methyl vinyl ether methoxyethylene
  • M.W. molecular weight
  • These copolymers are available for example as Gantrez AN 139 (M.W. 500,000) , AN 1 19 (M.W. 250,000) and S-97 Pharmaceutical Grade (M.W. 70,000) , of GAF Chemicals Corporation.
  • operative polymers include those such as the 1 ⁇ 1 copolymers of maleic anhydride with ethyl acrylate, hydroxyethyl methacrylate, N-vinyl-2-pyrollidone, or ethylene, the latter being available for example as Monsanto EMA No. 1 103, M.W. 10,000 and EMA Grade 61, and 1 ⁇ 1 copolymers of acrylic acid with methyl or hydroxyethyl methacrylate, methyl or ethyl acrylate, isobutyl vinyl ether or N-vinyl-2-pyrrolidone.
  • Suitable generally are polymerized olefinically or ethylenically unsaturated carboxylic acids containing an activated carbon-to-carbon olefinic double bond and at least one carboxyl group, that is, an acid containing an olefinic double bond which readily functions in polymerization because of its presence in the monomer molecule either in the alpha-beta position with respect to a carboxyl group or as part of a terminal methylene grouping.
  • Such acids are acrylic, methacrylic, ethacrylic, alpha-chloroacrylic, crotonic, beta-acryloxy propionic, sorbic, alpha-chlorsorbic, cinnamic, beta-styrylacrylic, muconic, itaconic, citraconic, mesaconic, glutaconic, aconitic, alpha-phenylacrylic, 2-benzyl acrylic, 2-cyclohexylacrylic, angelic, umbellic, fumaric, maleic acids and anhydrides.
  • Other different olefinic monomers copolymerizable with such carboxylic monomers include vinylacetate, vinyl chloride, dimethyl maleate and the like. Copolymers contain sufficient carboxylic salt groups for water-solubility.
  • a further class of polymeric agents includes a composition containing homopolymers of substituted acrylamides and/or homopolymers of unsaturated sulfonic acids and salts thereof, in particular where polymers are based on unsaturated sulfonic acids selected from acrylamidoalykane sulfonic acids such as 2-acrylamide 2 methylpropane sulfonic acid having a molecular weight of about 1,000 to about 2,000,000, described in U.S. Pat. No. 4,842,847, Jun. 27, 1989 to Zahid, incorporated herein by reference.
  • polyamino acids particularly those containing proportions of anionic surface-active amino acids such as aspartic acid, glutamic acid and phosphoserine, as disclosed in U.S. Pat. No. 4,866,161 Sikes et al., incorporated herein by reference.
  • the thickening agents are carboxyvinyl polymers, carrageenan, xanthan gum, hydroxyethyl cellulose and water soluble salts of cellulose ethers such as sodium carboxymethyl cellulose and sodium carboxymethyl hydroxyethyl cellulose.
  • Natural gums such as karaya, gum arabic, and gum tragacanth can also be incorporated.
  • Colloidal magnesium aluminum silicate or finely divided silica can be used as component of the thickening composition to further improve the composition′s texture.
  • thickening agents in an amount of about 0.5%to about 5.0%by weight of the total composition are used.
  • Natural calcium carbonate is found in rocks such as chalk, limestone, marble and travertine. It is also the principle component of egg shells and the shells of mollusks.
  • the natural calcium carbonate abrasive of the invention is typically a finely ground limestone which may optionally be refined or partially refined to remove impurities.
  • the material has an average particle size of less than 10 microns, e.g., 3-7 microns, e.g. about 5.5 microns.
  • a small particle silica may have an average particle size (D50) of 2.5 -4.5 microns.
  • natural calcium carbonate may contain a high proportion of relatively large particles of not carefully controlled, which may unacceptably increase the abrasivity, preferably no more than 0.01%, preferably no more than 0.004%by weight of particles would not pass through a 325 mesh.
  • the material has strong crystal structure, and is thus much harder and more abrasive than precipitated calcium carbonate.
  • the tap density for the natural calcium carbonate is for example between 1 and 1.5 g/cc, e.g., about 1.2 for example about 1.19 g/cc.
  • polymorphs of natural calcium carbonate e.g., calcite, aragonite and vaterite, calcite being preferred for purposes of this invention.
  • An example of a commercially available product suitable for use in the present invention includes 25-11 FG from GMZ.
  • Precipitated calcium carbonate is generally made by calcining limestone, to make calcium oxide (lime) , which can then be converted back to calcium carbonate by reaction with carbon dioxide in water.
  • Precipitated calcium carbonate has a different crystal structure from natural calcium carbonate. It is generally more friable and more porous, thus having lower abrasivity and higher water absorption.
  • the particles are small, e.g., having an average particle size of 1 -5 microns, and e.g., no more than 0.1%, preferably no more than 0.05%by weight of particles which would not pass through a 325 mesh.
  • the particles have relatively high water absorption, e.g., at least 25 g/100g, e.g. 30-70 g/100g. Examples of commercially available products suitable for use in the present invention include, for example, 15 Plus from Lagos Industria Quimica.
  • the invention may comprise additional calcium-containing abrasives, for example calcium phosphate abrasive, e.g., tricalcium phosphate (Ca 3 (P0 4 ) 2 ) , hydroxyapatite (Ca 10 (P0 4 ) 6 (OH) 2 ) , or dicalcium phosphate dihydrate (CaHP0 4 ⁇ 2H 2 0, also sometimes referred to herein as DiCal) or calcium pyrophosphate, and/or silica abrasives, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite or other siliceous materials, or combinations thereof.
  • calcium phosphate abrasive e.g., tricalcium phosphate (Ca 3 (P0 4 ) 2 ) , hydroxyapatite (Ca 10 (P0 4 ) 6 (OH) 2 ) , or dicalcium phosphate dihydrate (CaHP0 4 ⁇ 2H 2 0, also sometimes
  • silica suitable for oral care compositions may be used, such as precipitated silicas or silica gels.
  • silica may also be available as a thickening agent, e.g., particle silica.
  • the silica can also be small particle silica (e.g., Sorbosil AC43 from PQ Corporation, Warrington, United Kingdom) .
  • the additional abrasives are preferably not present in a type or amount so as to increase the RDA of the dentifrice to levels which could damage sensitive teeth, e.g., greater than 130.
  • Water is present in the oral compositions of the invention.
  • Water employed in the preparation of commercial oral compositions should be deionized and free of organic impurities.
  • Water commonly makes up the balance of the compositions and includes 5%to 45%, e.g., 10%to 20%, e.g., 25 -35%, by weight of the oral compositions.
  • This amount of water includes the free water which is added plus that amount which is introduced with other materials such as with sorbitol or silica or any components of the invention.
  • the Karl Fischer method is a one measure of calculating free water.
  • humectant to reduce evaporation and also contribute towards preservation by lowering water activity.
  • Certain humectants can also impart desirable sweetness or flavor to the compositions.
  • the humectant, on a pure humectant basis, generally includes 15%to 70%in one embodiment or 30%to 65%in another embodiment by weight of the composition.
  • Suitable humectants include edible polyhydric alcohols such as glycerine, sorbitol, xylitol, propylene glycol as well as other polyols and mixtures of these humectants. Mixtures of glycerine and sorbitol may be used in certain embodiments as the humectant component of the compositions herein.
  • compositions of the present disclosure contain a buffering agent.
  • buffering agents include anhydrous carbonates such as sodium carbonate, sesquicarbonates, bicarbonates such as sodium bicarbonate, silicates, bisulfates, phosphates (e.g., monopotassium phosphate, dipotassium phosphate, tribasic sodium phosphate, sodium tripolyphosphate, phosphoric acid) , citrates (e.g. citric acid, trisodium citrate dehydrate) , pyrophosphates (sodium and potassium salts) and combinations thereof.
  • phosphates e.g., monopotassium phosphate, dipotassium phosphate, tribasic sodium phosphate, sodium tripolyphosphate, phosphoric acid
  • citrates e.g. citric acid, trisodium citrate dehydrate
  • pyrophosphates sodium and potassium salts
  • the amount of buffering agent is sufficient to provide a pH of about 5 to about 9, preferable about 6 to about 8, and more preferable about 7, when the composition is dissolved in water, a mouthrinse base, or a toothpaste base.
  • Typical amounts of buffering agent are about 5%to about 35%, in one embodiment about 10%to about 30%, in another embodiment about 15%to about 25%, by weight of the total composition.
  • the present invention in its method aspect involves applying to the oral cavity a safe and effective amount of the compositions described herein.
  • compositions and methods according to the invention can be incorporated into oral compositions for the care of the mouth and teeth such as toothpastes, transparent pastes, gels, mouth rinses, sprays and chewing gum.
  • MeSA Direct detection and quantification of MeSA in aqueous solution is challenging due to its low water solubility. While 1 H NMR provides structural and quantitative information of the specific substrate in the aqueous mixture, the greatest limitation of NMR is its poor sensitivity. MeSA was present in the test solution at a concentration of 3.29 mM. Typically, a high concentration of substrate is needed for NMR quantitative analysis. However, to quantify a substrate by NMR at concentrations at or below about 0.1 wt. %in water is not possible without effective solvent suppression. To overcome this hurdle, composite ⁇ /2 pulses were applied prior to pre-saturation pulses to effectively suppress the water peak of the sample.
  • the resonances corresponding to protons of MeSA, salicylate acid (SA) , glycine (Gly) , and methanol can be identified, as indicated in Fig. 1.
  • the starting spectrum of MeSA consists of a methyoxy group (-OCH 3 , labeled 5) centered at 3.77 ppm, and four lines corresponding to phenol protons located between 6.7 and 7.7 ppm (labeled 1, 2, 3, 4) .
  • the peak intensity corresponding to the methyoxy group of MeSA clearly reduced by about 30%, while the peak corresponding to methanol at 2.7 ppm starts to appear.
  • the phenolic hydroxyl group of neutral MeSA in the ortho position is unique in affecting the cleavage of the ester group due to the formation of intramolecular hydrogen bonding with an oxygen of adjacent carboxyl group.
  • This intramolecular hydrogen bond can also be formed by solvent.
  • this hydrogen bond in the MeSA is believed to increase the positive charge of the MeSA’s carbonyl carbon, thereby making it more prone to act as a good electrophile for the ester hydrolysis reaction of MeSA.
  • the intramolecular hydrogen bonds no longer exist (e.g. methyl paraben or methyl benzoate) . In such a case, the ester hydrolysis of MeSA does not occur, even in the presence of Gly at higher pH. This finding suggests that intramolecular hydrogen bonding of MeSA plays a major role in the MeSA hydrolysis.
  • FIG. 4 clearly shows that Gly can significantly accelerate the ester hydrolysis of MeSA in aqueous solution.
  • 1 H NMR spectra of MeSA with and without Gly at pH 9.0 were acquired prior hydrolysis, as shown in Fig. 5.
  • a notable change in the chemical shift pattern of protons corresponding to the meta position of MeSA’s benzene ring (labeled 2, 4) was observed with and without Gly.
  • 1 H chemical shift of Gly in the presence of MeSA has a 0.2 ppm downfield shift at pH 9.0.
  • MeSA hydrolysis rate is much faster than that of MeSA alone, but was slower than that of MeSA with Gly.
  • MeSA hydrolysis rate was slightly faster than that of MeSA only, but not as fast as that of Boc-Gly-OH sample.
  • the protecting groups can fully mask the amine and carboxyl groups of Gly to make both groups unavailable to interact with MeSA, so that the hydrolysis rate of MeSA with Boc-Gly methyl ester is the same as that of MeSA without Gly.
  • the availability of their unmasked groups depends on their pKa and pH. From a consideration of the pKa values, the pKa of the amine and carboxyl group of Gly is 9.6 and 2.3, respectively.
  • Dentifrices were created according to the following formulations:
  • the Formulations above were created by first adding sodium saccharin, sodium monofluorophosphate and water to a beaker. The contents are allowed to dissolve. Glycerin, carboxymethyl cellulose and tetrasodium pyrophosphate are added and mixed for 5 minutes to form a gel. Then, sodium fluoride, arginine and phosphoric acid are added, and mixed for 20 minutes. The contents are transferred to a Ross pot, dicalcium phosphate dihydrate is added and mixed for 10 minutes. Thickener silica (i.e., Zeodent 165) is added and subsequently mixed for 10 minutes. Finally, sodium lauryl sulfate powder, colorants and flavorants are added mixed for 5-10 minutes to obtain finished dentifrice products.
  • Glycerin, carboxymethyl cellulose and tetrasodium pyrophosphate are added and mixed for 5 minutes to form a gel. Then, sodium fluoride, arginine and phosphoric acid are added, and mixed for 20 minutes. The contents are
  • the dentifrice composition was packaged in a tube and placed in an environment to simulate accelerated aging (49°C environment) over six weeks.
  • the aged compositions i.e., formulations 1 and 2 were used for wintergreen flavor analysis by gas chromatography-mass spectrometry (GC-MS) , described below.
  • GC-MS gas chromatography-mass spectrometry
  • Formulations 1 and 2 were tested for Wintergreen Flavor quantitation using GC-MS. 1g of each of Formulation 1 and 2 was weighed to a 50 mL Polypropylene Conical Tube. 1g of water was added into each tube and mixed with the Formulations until slurries were formed. Next, 8g of N-propanol and Iso-octane were added and was mixed again. The solutions were then allowed to rest. The clear solution was transferred into a GC autosampler vial for GC-MS analysis.
  • Wintergreen oil standards were also created. 100mg Wintergreen Oil was added into 49.9g 1 ⁇ 8 ⁇ 15 Water-N-propanol-Iso-octane solution. The total weight of the solution was 50g. This solution was the stock wintergreen oil solution. The concentration of the stock solution was 2000 ppm. Then, the stock wintergreen oil solution was diluted three-fold, four-fold, and six-fold with 1 ⁇ 8 ⁇ 15 Water-N-propanol-Iso-octane Solution, reaching target concentrations of 333 ppm, 500 ppm, and 666 ppm. Standard solutions of those three target concentrations were transferred into ROBO.
  • the oven temperature was ramped to 150°C at a rate of4°C min-1 and held for 2.33 min.
  • the total GC running time is 20 min.
  • the carrier gas was helium and the flow-rate was set at 1 mL min-1.
  • the identification of wintergreen flavor was accomplished by comparing the GC retention time and the pure commercial wintergreen flavor standards.
  • the quantitative total ion count (TIC) scan was set for methyl salicylate and other ingredient identification.
  • the total ion integration from m/z 45 to 450 was monitored and used for quantitation.
  • the data integration was performed by using a ChenStation data acquisition system (Agilent Technology, Palo Alto, CA, U.S.A. ) .
  • Table 2 Methyl Salicylate degradation percentage and total wintergreen flavor recovery percentage after standardized toothpaste aging study (6 weeks at 49C) .

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Abstract

Une composition d'hygiène buccale stabilisée comprend des acides aminés et des composants d'arôme traditionnellement incompatibles. L'invention concerne également des procédés de préparation et d'utilisation.
EP19926062.1A 2019-04-25 2019-04-25 Compositions d'hygiene buccale et leurs méthodes d'utilisation Pending EP3946639A4 (fr)

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GB1469398A (en) * 1973-05-21 1977-04-06 Oral Health Prod Inc Dental treatment
US4314990A (en) * 1979-10-15 1982-02-09 The Procter & Gamble Company Toothpaste compositions
US4272513A (en) * 1980-01-31 1981-06-09 Colgate-Palmolive Company Stabilized oral composition
US5284659A (en) * 1990-03-30 1994-02-08 Cherukuri Subraman R Encapsulated flavor with bioadhesive character in pressed mints and confections
US8007771B2 (en) * 2006-07-07 2011-08-30 The Procter & Gamble Company Flavors for oral compositions
MX2009003235A (es) * 2006-09-29 2009-04-08 Procter & Gamble Composiciones orales que contienen redes de gel.
AU2012396294B2 (en) * 2012-12-05 2015-06-11 Colgate-Palmolive Company Fluoride-stable zinc containing oral care compositions
AU2012397267B2 (en) * 2012-12-19 2015-10-08 Colgate-Palmolive Company Oral care compositions comprising zinc amino acid halides
EP3046532B1 (fr) * 2013-09-17 2019-08-14 Colgate-Palmolive Company Composition de soin buccal
WO2016106069A1 (fr) * 2014-12-23 2016-06-30 Colgate-Palmolive Company Composition pour soins buccaux
CN106236612B (zh) * 2016-08-27 2020-06-26 广东罗浮山国药股份有限公司 一种牙膏及其制备方法
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